Three months ago Monday, the Cleveland Cavaliers became the 2015-16 NBA champions. Five weeks from Tuesday, the Cavs will begin the 2016-17 regular season and the grueling effort to defend their crown. As the new season nears and nears, the team’s most intriguing offseason question remains unanswered: What will happen with J.R. Smith?

But as for Smith’s next NBA contract, there hasn’t been much activity at all. He’s had a handful of offseason interviews, explaining his perspective on the contract negotiations. It’s been announced that he won’t be at the team’s training camp in California this week. And the preseason and regular season keep getting closer and closer.

So, where do things stand now? Let’s take a look at the whole situation for the parties involved and see where things might land in the coming days, or perhaps weeks.

The Tristan Thompson Negotiations, Part Duex

Of course, last summer, the Cavs found themselves at an impasse with another player represented by the same agent who now represents J.R. Smith. That agent, of course, is Klutch Sports Group’s Rich Paul. And as is well known everywhere, Paul is LeBron James’ long-time close friend. To what extent James actually is involved with the agency, it remains somewhat vague. But it’s hard not to immediately see the similarities in these situations and to point out Paul’s fascinating young history as a player-agent.

Cavs big man Tristan Thompson, coming off his rookie contract, finally signed his new five-year $82 million deal on Oct. 21, 2015. He missed the entirety of last season’s training camp, media day and the seven-game preseason schedule. He only returned to the team with less than a week to go until Opening Night, Oct. 27, at the United Center against the Chicago Bulls.

In fact, this actually is the third straight offseason with Rich Paul at the center of a long contract negotiation impasse. In 2014, Phoenix Suns guard Eric Bledsoe, also just finishing his rookie contract, didn’t sign his new five-year $70 million deal until Sept. 24. The back-and-forth between player/agent and organization got a bit contentious over those five months of the playoffs-less offseason.

But through those two very public situations, Paul likely gained some notoriety around the league for being a strong and patient negotiator on behalf of his clients. The Klutch Sports Group agency nabbed Washington Wizards All-Star John Wall, No. 1 draft pick Ben Simmons of the Philadelphia 76ers and also J.R. Smith himself already this calendar year.

While represented by CAA last summer, Smith botched his free agency by declining his $6.4 million player option and then only receiving $5 million in a new deal with the Cavs. He grossly over-estimated his value on the open market at the time and then finally re-signed at a lower rate around Labor Day. So you can certainly expect Smith is looking for a big payday this time around. And Rich Paul has proven he will be there to back him every step of the way.

Looking at J.R. Smith’s perspective

Smith, who was the No. 18 pick in the 2004 NBA Draft and ranks No. 17 in the NBA’s all-time three-point leaderboard, has made only $45.5 million in career contract earnings, according to Basketball-Reference.com. His largest single-season payday was $6.8 million with the Denver Nuggets during the 2010-11 season.

After playing stellar two-way basketball all season long and winning a championship ring, life is undoubtedly different now for J.R. Smith. He’s shed the weight of the bad-boy days from his previous stops around the league. He also had several significant life moments happen during this offseason already, which has likely shaped his open attitude toward free agency in his public comments thus far.

But only a small handful of teams still have eight-figure salary cap space after July’s massive free agency spending spree. And those teams – Brooklyn, Denver, Philadelphia and Phoenix, per Albert Random’s cap site – are the longest of long shots to have any title hopes this coming season. That means the Cavaliers, who own his Bird rights, by far remain his most logical destination.

During that July free agency frenzy, Smith certainly saw a number of similar players receive mega-sized new contracts. It’s not hard for any professional player to open their eyes and compare oneself to their peers on the open market. Here are just four that seem to be decent comparisons:

Jamal Crawford – Turns 36-and-a-half today. Was the No. 8 pick in the 2000 NBA Draft. The league’s first three-time Sixth Man of the Year, he’s carved out an impressive niche as a bench super-scorer for the oft-good-but-not-great Los Angeles Clippers. He is a career 15.5-point scorer and ranks No. 7 on the NBA’s all-time three-point leaderboard. He re-signed with the Clippers on a three-year $42 million deal. The third year only has $3 million guaranteed.

Courtney Lee – Turns 31 in October. Was the No. 22 pick in the 2008 NBA Draft. A thorn in the Cavs’ side during the 2009 Eastern Conference Finals, he was a valuable contributor for the Memphis Grizzlies and the Charlotte Hornets last season. But after the Hornets prioritized retaining free agents Nicolas Batum and Marvin Williams, the career 9.6-point scorer landed a big four-year $48 million deal with the New York Knicks.

Arron Afflalo – Turns 31 in October. Was the No. 27 pick in the 2007 NBA Draft. A solid defender and career 11.6-point scorer, he was Lee’s predecessor on the wing for the Knicks last season. He also was traded from Orlando to Denver in June 2014, then from Denver to Portland at the 2015 trade deadline. Afflalo signed a two-year $25 million deal with the Sacramento Kings this offseason. The second season only is guaranteed for $1.5 million.

Eric Gordon – Turns 28 on Christmas Day. Was the No. 7 pick in the 2008 NBA Draft. A career 16.6 point-scorer, he’s averaged only 52 games played per season in his career due to a large assortment of injuries. Despite that risk, he still received a handsome four-year $53 million deal with the Houston Rockets. The deal was just shy of the four-year $58 million deal he signed back in 2012 with New Orleans, which was largely considered a bust because of his many injuries.

Something I’ve said to friends on several occasions this offseason: If I was J.R. Smith, I’d be waiting to receive $42 million guaranteed, no matter what. Cleveland.com’s Joe Vardon believes Smith is looking for a deal with $15 million annually. Crawford, who is five-and-a-half years his senior, received $42 million, albeit with a small guarantee in the third year. Lee and Gordon, who rate similarly, received over $50 million guaranteed and a fourth fully guaranteed year.

In a best-case scenario for J.R. Smith, he’d top all four of these players with a fully guaranteed four-year $54 million deal. Or otherwise, if the team prefers this instead, maybe three years and $48 million. That’d prove his standing as one of the league’s preeminent two-way wings. It’d reward his great play and solid behavior with the Cavaliers after a botched negotiation last offseason. And it would more than double his career earnings thus far in the NBA.

Smith and Rich Paul are likely just playing the long game in this negotiation, as any player and his agent should. Far too often in North American professional sports, teams receive the upper-hand in contract negotiations due to fan pressure to sign early and end any possible contentiousness. But in this case, by waiting and waiting patiently for likely $40 million-plus guaranteed and at least three fully guaranteed seasons, Smith is probing to see how far the Cavs are willing to go.

Looking at the Cavaliers’ perspective

As stated above, the Cavaliers are the most logical destination for J.R. Smith. By owning his Bird rights, they can offer him as much money as allowed for a player of his veteran status in the league. And since no other playoff contender has that significant of cap space, this should be an easy negotiation, right?

Not exactly. Any sports team of any kind, just like any business, likely operates with some semblance of a budget. Since we do not know the actual financials of the Cavaliers, there are only so many resources at our disposal. One such resource: The exact amount of money spent on player salaries and the luxury tax during the 2015-16 season. This, of course, was before the league’s gigantic cap increase that just occurred.

Following the league’s audit in July, ESPN’s Marc Stein reported that the Cavs officially paid $54 million in luxury taxes. Working backwards using last season’s $84.7 million luxury tax line and my CBA tax calculator, you can then estimate that the 2015-16 Cavaliers spent about approximately $161.1 million on player-related expenditures.

So, where do the 2016-17 Cavaliers stand right now? According to The Vertical’s Bobby Marks, the Cavs have $115.5 already guaranteed for just 13 players on the roster. That figure does not include the unguaranteed training camp invites given to DeAndre Liggins, Markel Brown, Eric Moreland and John Holland.

Let’s then assume the Cavs eventually fill a 14th roster spot with some veteran minimum player. Per Larry Coon’s CBA FAQ, and as illustrated by Marks’ math and a previous clarification, only a max of the two-year veteran minimum is attributed to the team’s salary cap in such a case. The remaining amount is reimbursed by the league. So that would add another $980,431 to the player-salary bill, at a most.

Adding in that mystery veteran player, that then would put the Cavs at $116.5M for 14 players. The tax line for the 2016-17 season jumped all the way up to $113.3M. The Cavs would thus already be $3.2M above the tax line already, before even adding in any salary amount for J.R. Smith. The non-repeater tax penalty for being that far over the line is $4.8M, using my CBA tax calculator.

Here is then how the team’s tax bill and overall player-related expenditures change based on the amount given to J.R. Smith for the 2016-17 season:

$5 million to J.R. Smith: Extra $8.3 million in taxes and $134.5 million total spending

$8 million to J.R. Smith: Extra $14.4 million in taxes and $143.6 million total spending

$10 million to J.R. Smith: Extra $19.4 million in taxes and $150.6 million total spending

$12 million to J.R. Smith: Extra $24.5 million in taxes and $157.8 million total spending

$14 million to J.R. Smith: Extra $31 million in taxes and $166.3 million total spending

$16 million to J.R. Smith: Extra $37.5 million in taxes and $174.8 million total spending

As one can quickly tell, and as I’ve illustrated in multiple past occasions – here, here and here, for starters – the NBA’s progressive luxury tax system quickly adds up once you’ve passed the threshold. For every dollar given to J.R. Smith, the Cavs will be taxed at a rate between 150-250 percent. To match last year’s total spending, that would mean a 2016-17 contract of about $12.8 million for J.R.

Of course, this isn’t all that fair to J.R. It’s not his fault necessarily that the Cavs just happen to have their entire roster already built out for this upcoming season and he’s the last one to sign. Inherently, that shouldn’t force him to accept a lesser contract. But the math is the math. The Cavs will likely be adding more than $20 million to their total spending this season because of the incremental effect of J.R. Smith’s new deal.

In terms of long-term flexibility, the Cavs also likely are looking to hold on to any semblance of cap freedom as they can. Between just LeBron James (player option), Kevin Love, Kyrie Irving, Tristan Thompson and Iman Shumpert, the Cavs already have over $108 million in player salaries set aside for the 2018-19 season. If they give J.R. Smith a fully guaranteed third year, that could jump over $120 million already.

Based on current projections, that could easily be well over the luxury tax line. And although the Collective Bargaining Agreement will be renegotiated next summer, the Cavs could still stand the risk of facing the even more punitive repeater tax brackets shortly. Quickly, the Cavs might not have any financial flexibility for free agency moves or trade dumps for three full years, or more.

So it’s also easy to see that the Cavs are in a delicate situation here too. Teams like to reward their own players for great play and good service. But the numbers are adding up very quickly. They can’t necessarily plan on finding a miraculous Anderson Varejao-for-Channing Frye cost-saving and roster-improving move every season. They won’t be so lucky every time into the future.

What comes next

Now, I’m not trying to tell anyone how to be a fan. As fans, we all would like the Cleveland Cavaliers to do as well as possible on the basketball court this coming season. That pretty much exclusively requires J.R. Smith signing a new contract at some point soon. There’s no other sensible way to replace his two-way production given the team’s roster and payroll situation.

But I do think it’s perfectly reasonable that it has taken so long for these two sides to reach an agreement. One could easily point out that Dan Gilbert’s real-time net worth is $4.6 billion and the Cavaliers organization likely made millions off the championship run and related merchandise. Those are both fair points. Gilbert still likely wants to run his business as a business. And that means setting practical budgets, even if it fans don’t agree with every single move and negotiation tactic.

Yes, Gilbert gave LeBron James his promise to not cut any corners when James returned to the franchise in 2014. Still, there likely remains a ceiling of some kind for the team’s willingness to spend historic amounts of money on its basketball product. That likely has factored into the impasse with J.R. Smith and Rich Paul this offseason. Many fans might not enjoy this part of basketball analysis and I’m not one to force them too. But it’s the practical reality of the situation as it stands currently.

Where will it go from here? I’d imagine the sides will meet somewhere in the middle, as always tends to happen in situations like this. Maybe Smith won’t receive that fourth year. Maybe he’ll still receive a guarantee of $40 million in some way. But I’d still figure that he’ll be in a Cavaliers Wine & Gold uniform come Opening Night and the ring ceremony at The Q on Tuesday, Oct. 25.

Jacob Rosen is a long-time contributor to WaitingForNextYear. He's written for the site since his freshman year at the University of Dayton back in spring 2009. Now, Jacob lives in New York City where he works for the sports business startup KORE Software. You can follow him on Twitter at @JacobLRosen .

CB, I think you make a really strong point about the potential emptiness of my and others moral concerns. And it is one I constantly evaluate. I have tried to quit the NFL/college football a couple of times and continue to enjoy it despite knowing the consequences to players. And if we cannot be dissuaded […]

That last line is particularly important.Your odds of becoming a pro football player if you play in high school is approximately 1 in 1,200. Those kids mashing their bodies up playing for Glenville are likely to never get paid a dime for it, and are taking very long odds.